A Lifetime of Hope and Regret

It’s easy to get lost. To look around and suddenly find yourself wondering how you got here — and why it seems so far from where you thought you’d be. What wrong turn did you take? Is there still time to go back and start again? To be the person you wanted to be? To do the things you want to do?

One day becomes a year, which quickly turns into a decade. Before you know it, you’re miles from the life you imagined.

“Tomorrow,” you say to yourself. “Tomorrow, I’ll fix things.”

But tomorrow comes and goes and you continue down the same path, caught up in the surging river that is life.

Reading entries for my round-the-world trip contest brought regret to the forefront of my mind. I saw so much of it from the strangers who entered; strangers who poured their heart out to me about loss, pain, suffering, snuffed-out dreams, and second chances.

Yet beneath all the worry, regret, and sadness, there was hope.

The desire for a new beginning. A chance to be the person they wanted to be; to find purpose in their life; to escape a future they didn’t want — but one that felt so inevitable.

When you ask people why they want to travel the world, and 2,000 people come back with stories that all end with a version of “to start fresh,” it brings this obvious but forgotten realization back into your mind.

My own life is a minefield of regret — both big and small: Regret at not traveling sooner, partying too much, never becoming fluent in a foreign language, never studying abroad, letting a certain relationship slip away, not staying in touch with friends, not saving more, not moving slower, and not following my gut. Then there are the day-to-day regrets — things like not closing my computer 30 minutes earlier or reading more or laying off those french fries more. There are countless regrets.

In thinking about our own issues, we often forget that everyone around us is fighting their own inner battles. That the grass is never truly greener. That when someone is snappy at you in the grocery store, short with you at the office, or sends you a nasty, trolling email, they, like you, are dealing with their own inner demons.

They, like you, think of second chances, missed opportunity, and unfulfilled dreams.

We’re taught by society to avoid “a lifetime of regret.” “Have no regrets!” is our mantra. But I think regret is a powerful motivator. It is a teacher, a manual to a better life.

Regret teaches us where we went wrong and what mistakes to avoid again.

Reading these entries initially weighed me down. I couldn’t help but think, “There’s a lot of unhappy people out there.”

But the more I thought about it the more I realized they weren’t unhappy. Yes, there was regret, pain, and sadness in those contest entries — but there was also a lot of hope, determination, and energy. These entrants were not going to wallow in regret. They were looking for a way to move forward. They felt inspired, motivated. Many promised that no matter the outcome of their entry, they were determined to make a change.

Reading these entries taught me that regret, it turns out, is life’s best motivator. Two thousand people said, “Not again — I won’t do this twice!”

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What an insightful article! Truly a great read. I’m a bit older to have no regrets, I have a few! But I’m finding getting ready for my first big travel to learn from other’s mistakes by reading for the ultimate goal of doing it myself. Like someone said already, “no one said you had to sprint!”. I’m sad I waited so long in life to experience the world but I am ready to begin a journey of a lifetime. Thanks again for your commentary!

Well written Matt. What if we all took a moment and listed our regrets and then made a plan to do something we will never regret to match. While they may not cancel each other out, our lives will be more fullfilled with more hope, more love, more Travel, and pray much less regret moving forward.

My take on regret; feel it if it’s there then let it go, forever. Let it go permanently by diving into fears that lead you to your dreams. Do not hesitate. Book the trip even though you feel afraid to travel. Book the trip even though fam and friends will criticize you for leaving your family. Book the trip despite everybody telling you it’s a mistake.

We don’t do regrets here. Which is why we are happy. But in human moments if regret arises I feel it, let it go and move in the opposite direction, toward my fun, freeing dreams, even if it means wading through fears. Always does 😉

This article spoke to me in more ways than I can express. I’ve said it a million and one times before- regret is a POWERFUL tool. The notion that we should live life without regrets is phony and in a sense, dangerous because it forces many people to mask their true feelings. I don’t subscribe to such mantra because it’s neither healthy nor realistic. Certainly, having a life marred with regrets is one thing or constantly living with regrets, but asking one to live without regrets is essentially asking the person to live in a bubble. A life well lived has its ups and downs, regrets and satisfactions and everything in between. The question is, how do you forge ahead in spite of that regret or those regrets? That is where hope comes into play. Hope like regret is equally a POWERFUL tool because it forces us to evaluate things while holding on. However, we might find it difficult to have hope if we insist on punishing ourselves for a mistake/regret. In my experience, regretting certain decisions/choices has certainly molded me into a better person and it has also made me stronger mentally and in other aspects. In other words, our regrets/mistakes can either make us or break us- it’s a choice we have to make for ourselves. When things get hard and you find yourself struggling, please reach out (to a reputable professional or trusted source) for help. Trying to do it all alone is sometimes how people go from “basic” regret to depression to mental breakdown and possibly worse. Overall, I believe that regret is a teacher for those who are willing to be vulnerable, acknowledge their mistakes and willing to put in the work needed to overcome the source of the regret and the regret itself. It is not a punishment or sign of weakness; it is merely part of something called being human. So people should not demonize or dehumanize themselves for having a human experience. Just live, learn and thrive and never stop being the best version of YOU.

It was border line creepy this popping up in my emails after my experiencing real regret for the first time yesterday. I bought a bottle of liqueur that I shouldn’t have ($$) and felt like death because of it which is odd in itself. Im 18 and just graduated high school with no qualifications, and have been trying really hard to get over seas by working and so far everything has gone wrong- but I still havent regretted any of it. Maybe its because im young or maybe its the universe telling me im still destined for great places. I just don’t want to feel the way I do about this bottle of alcohol when it comes to “really living”.

Robert Frost wrote a poem about the road not taken. I read it in my high school years and have tried to live my life not regretting any path not taken, but rather being more determined to take the paths I want to! I’m 61 now, and my husband and I have been retired a couple of years and have travelled Turkey, Africa and Central Asia since then. Regrets, maybe but not enough to mention! There are so many wonderful quotes out there, but one of my favourites is from Forrest Gump “ Life is like a box of chocolates….” and there are only so many chocolates in the box…so make the most of each one you choose! One minute you are in your twenties travelling through Asia and before you know it you are in your sixties! So much to do, so little time! Don’t worry too much about what you haven’t done, just enjoy all the experiences you can while you can…you never know what is around the corner!

“In a world where death is the hunter, my friend, there is no time for regrets or doubts. There is only time for decisions.” – Carlos Castaneda

I have always pretty much looked upon regret this way. With every path you choose, regrettable happenstances will be on it. As you said, no need to dwell and wallow in regret. One can have clarity and not make mistakes without using regret as the impetus to do so. Life is the journey and it is always better than the destination. Platitudes in place… I’m out;)

Matt, It’s so easy to be a Monday morning quarter back would’ve, could’ve, should’ve! The bottom line is everything we have gone through and done shaped us into who we are good and bad. With regard to travel, it’s fasionating to me how many people say “ I always wanted to travel” but they never put a plan in motion. The “someday” folks I don’t get. I want to believe people do/have whatever they value or want in life. Children, marriage, travel on and on! It’s about what you want and how to get it, putting the wheels in motion. I worked a minimum wage job when I first started traveling. Disposable income where you want it to go. What’s important to YOU?

Great article! At 75, yes, there are many regrets, but some victories also. It’s those successes that make me glad that Matt and so many other young people are experiencing our world. There is no better education.

Glad you had an opportunity to share. After reading about all the gap year travelers, world travelers who didn’t go into a corporate job the day after college and others who tell you about the ‘best of everything’ I no longer envy any of them.

We all travel differently and had I not worked 7 day a week jobs and lived simply I would NOT be traveling anywhere I want to go at anytime. These are different trips than vacations in my 20’s or time wasted on getting the ‘perfect tan’.

So I may regret not having this freedom 30 yrs ago I would NOT appreciate my slow travel meeting locals and experiencing the places I visit….

Wow this is so true. And I really feel like living a life without regret means you’re either not taking enough risks or you’re unable to look at yourself and your choices and evaluate whether you’re really pushing yourself to live the best possible life. While I think regret is always going to be a part of life, it’s also important that it goes hand-in-hand with gratitude.

Good column Matt. I suspect that the longer we live, the more time we have to accumulate regrets. Probably the biggest ones though are the ones you can’t go back and re-do; the children you never got around to having or the relationships that ended or you never got around to forming. If you didn’t get to see Asia at 25, you can likely still do it at 50. If you didn’t get around to having kids when you were young (or being a good parent to those you had) you can’t just do that when you’re older.

I’d say that the regrets of that nature are the ones perhaps that are the deepest and not possible to turn around.

I’m presently traveling for a year(quit the job, sold the house). Decided it was well past time to have some new experiences. I am well aware that we never know how much time we have left; lost 2 of my best friends when they were younger than I am now. It’s funny how many people just don’t get doing this; maybe if one is old enough to retire they accept it but before that they think it’s crazy and irresponsible.

“I’ll never know, and neither will you, of the life you don’t choose. We’ll only know that whatever that sister life was, it was important and beautiful and not ours. It was the ghost ship that didn’t carry us. There’s nothing to do but salute it from the shore.”

Cheryl Strayed writes beautifully and it is a sentiment that will resonate with almost everyone. What is your ghost ship?

Interesting article! Ultimately, we can travel all countries in the world, but as long as we haven’t embarked on our inner journey to transmute all our fears lurking in the vast subconscious lands of our mind, we will never really live. Once we start to live, we’ll put the spotlight on those regrets, and they will turn into shining gemstones, as we realise they were the very key to shape who we have become today. Go travel within to be able to travel without (regrets)!

Me too thinks that my life is a field of regrets. For the collegge I studied. For not taking the chances. For thinking you’re controler of life instead of life to accept to take you. Regret exists in religion as simple element of learning. Life is to be accepted, to be learned and grow. To dream more. I like the citation above that there’s no time for regrets, there’s only time for decision. We all can dream and are capable to achieve the goals if we want. That is the most important. To fulfill your life with goals. The most important thing that we learned as travelers is not to be attached. Thank you Matt for being who you are. You make my life a better place. I could just ignore you but you cannot be ignored.

Regret will always be a part of life Matt. Nobody can go thru life and avoid it completely or not have it impact them to one degree or another. There is a yang to every yin in life and the key to keeping our regrets small and more manageable is to know our priorities in life. People make poor decisions when they don’t know themselves.We can’t do everything perfectly all the time and we will sometimes make errors of judgement out of fear or ignorance when making any big decision.Choices have to be made between options and something must always be given up in order to attain something else. That is a fearful reality we all have to face sometimes.So in my opinion to sail thru our fears we need to cultivate courage in ourselves. Courage is not pretending we have no fear, but admitting we are afraid of a big change but still acting on our dreams because we know in our hearts that it is essential to our happiness.

I especially love this part of your post: “That when someone is snappy at you in the grocery store, short with you at the office, or sends you a nasty, trolling email, they, like you, are dealing with their own inner demons.”

I have been reading more about Buddhism recently, and it teaches so much about having compassion for others (and all living beings! #govegan). I’ve found that this idea of trying to understand where someone else is coming from really reduces my frustration with people and reminds me that we don’t know everyone’s story and it’s best to be as kind and compassionate as possible. For example, if someone cuts me off in traffic, I find it helpful to imagine they are rushing to meet a loved one at the hospital, or they had a bad day and just want to get home. That allows me to let go of any anger or frustration I may have initially felt toward them/their actions.

Thank you! I love reading things from like-minded people (it’s makes you feel a little more sane). I used to LOVE the concept of living life with “no regrets” but as time went on I began to realize that those “regrets” are a part of life that help to form you. Big or small, we all have things that we may wish we would have or would not have done; however, I believe, it’s actually quite a bit of pressure if you try to live with no regrets as a mantra because then you focus on the negatives of what you did wrong, as opposed to simply learning from you own life decisions. What matters most is not truly living with no regrets (because, come on), but rather, living in a way that we learn and grow from our past mistakes and make the next attempts even better. I think it’s so important to be able to treat our mistakes (or those of others) as learning experiences towards becoming the best versions of ourselves. It was such a refreshing reminder to see this point of view in your post, thanks!

Hey everyone! I just want to say thank for all your comments and stories. They were nice to read. I’m sorry I can’t respond to them all but I do enjoy them and it’s nice to hear your stories too. This community is a wonderful place!

This I know, I am in my mid-forties and is loving every minute what God has given me! I am not bragging but to give a chance to those, who are so worry about things that they do not have control over. Let go ….and let God do!

I been around the world, work on cruise ships, stay in London, NYC, and among other place, in my life time. Call me restless or a gypsy, been in love and been out of love for a long time….but I will tell you….I do not have ANY regrets!!!!

Such a powerful post Matt! I believe we’re all filled with regret, but that regret is such a powerful learning device. I wish we didn’t have to feel pain and sadness, but it’s those emotions that fuel us to think twice and do something different.

I loved reading this, it reminds me of my own shame, fear and regret. And to not just DO something about it, but to be kind to myself. Because everyone else is experiencing the same thing. And we could all just use a little more love <3

This is perfect. Regret has such a negative connotation, but I’ve never thought about how much it can change our futures for the better. It’s amazing that you read so many peoples’ stories and amazing that you were able to gain so much from them – and then share it with us. Thanks for this!

You must of been reading my mind. In a few months at the young age of 55, I will be able to retire. For the first time I will be free to do what I want and I am scared out of mind. However I will push through my fear because my dream has always to move out of the country for a year. I’ve already taken steps to make that dream a reality. Your article has just confirmed that I am all the right track.

June 30th (my last official day of work) will be my second chance. I’ve always taken the safe route and now that I will have unimaginable freedom, there will be no more regrets from that moment on.

I’m about halfway done my time on earth (at least according to the actuary tables!). My biggest regret is that even having so many choices in life, I still won’t be able to do all the interesting travel things I want to do like like living in dozens of countries, learning tons of languages, etc. but I realize how fortunate I am in life to be in this situation. After all, many people have no choices in life, due to their individual situations – family, culture, health etc. So really, instead of feeling regret, I like to just focus on the handful of travel and cultural experiences I can do in one lifetime. And to help others along the way with whatever skills and caring I can bring. (Great site, Matt!)

It’s great to read about different subjects other than travelling. I like your site because of this. You approach to travel is not like many others. You do not just show happy moments and how great traveller you are! but you also share this kind of insights. Thank you.

Brilliant post Matt. I think we all do carry regret. Its just human nature. Right from the small, I regret to eating that burger because now I feel sick right through to the bigger ones, I regret not going to Uni when I was younger. But you are dead right. Regret leads us to move forward, to be better and to make better decisions for ourselves. If we choose to. I know too many people who use their regrets to fuel misery in their lives which makes me feel sad for them.

An interesting perspective on regret. Even with all the awful mistakes I’ve made in life, I definitely don’t think I could place regret as one of my emotions. Yes, I’ve done dumb things, but those choices have put me where I am, and I guess I don’t want to have the negative emotion that the word regret carries.